Ethyl trimethylsilylacetate → HCID 21941242, compound

HRID 2216252Notes

Reaction equation

Br[C:2]1[CH:10]=[CH:9][C:8]2[C:4](=[CH:5][N:6]([CH2:11][CH:12]([CH3:14])[CH3:13])[N:7]=2)[CH:3]=1.C[Si]([CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])(C)C.CC(C)([O-])C.[K+].C(P(C(C)(C)C)C(C)(C)C)(C)(C)C>C1(C)C=CC=CC=1.C(OCC)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:23]([O:22][C:20](=[O:21])[CH2:19][C:2]1[CH:10]=[CH:9][C:8]2[C:4](=[CH:5][N:6]([CH2:11][CH:12]([CH3:14])[CH3:13])[N:7]=2)[CH:3]=1)[CH3:24]

Participants

Conditions

Temperature: 90 °C

Procedure

5-Bromo-2-(2-methylpropyl)indazole (1.41 g, 0.0056 mol) and palladium acetate (0.063 g, 0.00028 mol) were stirred in toluene (10 ml) under an atmosphere of nitrogen. Ethyl trimethylsilylacetate (2.35 ml, 0.0115 mol), potassium tert-butoxide (0.66 g, 0.059 mol) and a 10% w/v solution of tri-tert-butylphosphine in toluene (0.97 ml, 0.00048 mol) were added sequentially and then the mixture was heated to 90° C. for 105 minutes. The mixture was cooled to room temperature, diluted with diethyl ether and filtered through diatomaceous earth and the filtrate was evaporated in vacuo. The residue was purified by flash column chromatography on silica gel eluting with 2:1 diethyl ether:hexane to give ethyl[2-(2-methylpropyl)indazol-5-yl]acetate (1.85 g), as a yellow oil.

Workup

temperatureThe mixture was cooled to room temperature
filtrationfiltered through diatomaceous earth
customthe filtrate was evaporated in vacuo
customThe residue was purified by flash column chromatography on silica gel eluting with 2:1 diethyl ether

Sources & evidence

ORD record: ord-c42a42c0406b4ea293ec0e26aed7aaca
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07112553B1

Reaction notes

Loading…